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The story begins in New York City with the traditional Jewish marriage of emotionally shallow, self-absorbed, "nebbish"-man-boy Lenny Cantrow (Charles Grodin), a sporting goods salesman, to Lila (Jeannie Berlin, daughter of director Elaine May), an annoyingly unsophisticated and emotionally needy girl.

While on their honeymoon in Miami Beach, Lenny meets and pursues the beautiful but manipulative Kelly Corcoran (Cybill Shepherd), a Midwestern college girl on holiday with her parents. When Lila is severely sunburned, Lenny quarantines her to their hotel room as he engages in a series of rendezvous with Kelly, lying to Lila about his whereabouts. Lenny impulsively ends their ephemeral marriage to pursue an indifferent Kelly, his ideal woman and ultimate fantasy shiksa-goddess. He believes she is the girl he has been waiting for all of his life and just "timed it wrong."

After leaving Lila (after only five days of marriage), he follows Kelly to Minnesota, where her justifiably resentful and protective father (Eddie Albert) is a relentless obstacle. Mr. Corcoran has undisguised contempt of Lenny, even offering a $25,000 bribe for Lenny to leave following a dinner where Lenny inanely praises Midwestern produce as having "no deceit in the cauliflower." Lenny eventually marries Kelly, whose chief intent appears to be to rile and defy her father. At the wedding reception, Lenny's attempts at mingling with mindless conversation fails, and he is ignored by the guests, his bride, and the new in-laws. He is a stranger at his own feast, quoting the cliches of the Republican press to some unimpressed children and lapsing into the same useless hum with which Lila formerly drove him mad.[3] He got the girl, but appears to have lost a feeling of belonging.

The film is a black comedy, examining love and hypocrisy through a lens of pointed, subtle humor. Though it contains broad jokes, occasionally going for “laughs without shame,”[4]Elaine May is credited with emotionally grounding the film and providing “a real understanding of character” through eliciting the kind of “caustic, almost powerful humor that comes from moments of wincing recognition when human foibles are accurately captured and revealed.”[5] As another reviewer wrote in Sight & Sound, May’s strength lies in her “obsessive and affectionate observations of character.”[3]

May shares with her former comedy partner Mike Nichols a sparse, dialogue-oriented style and a quizzical perspective. She places an emphasis on character comedy; The Hollywood Reporter commented on her stylistic decisions to derive humor "from situations rather than obvious one-line jokes" and make comedic choices which "flow effortlessly from rhythmic dialogue, explosions of laughter."[6]The New Yorker's Pauline Kael wrote, "Elaine May has the rarest kind of comic gift: the ability to create a world seen comically."[7]

May's focus on comedic honesty, backlit by pain and misfortune, stylistically influenced a new generation of films. She pushed comedy into a "golden age as the result of the rise of the semi-surreal comedy of mishap, pain, insult, and desperation."[2]

The Heartbreak Kid is a particularly Jewish story; as Thomas Meehan wrote in The Saturday Review, the movie is a "triumph of New York Jewish humor,[8]" and The Village Voice called it "the culminating work of Hollywood's Jewish new wave."[9] All the filmmakers are Jewish—Friedman, Simon, May, the producer Edgar J. Schermick, and the composers Burt Bacharach and Hal David. The story follows Lenny Cantrow, the embodiment of the Jewish archetype of the "schemeil" (the schemer), as he dumps Lila (Jeannie Berlin), a "kvetchy Jew" and "sloppy, incipient yenta,"[10] for the girl of his dreams, an all-American WASP. The film is a deadpan fever dream of shiksa-chasing, taking place in what Bruce Jay Friedman dubs in the original short story as the land of “strange blonde people.”

The character of Lila in particular has been labelled extremely stereotypical; Film Quarterly likened her to a female Portnoy, publishing a review stating "Philip Roth's friendly anti-Semitism is strikingly similar to Friedman's."[10] Some critics have expressed concerns that the movie forwards a stilted vision of the modern female Jew and implicitly asks the question, "Why be married to a cloying, unsophisticated, slightly overweight Jewish girl (yenta) who speaks with a discernible sing-song Jewish intonation (Yiddish influence) when you can perhaps conquer a very Waspy-looking, knockout blonde shiksa type?"[11] This is despite the intentions of Jeannie Berlin, who told The New York Times that she did her best to honor the character and give Lila depth: "You see, I didn't want to make that girl stupid. It would have been so easy to do Lila stupid. I don't think Lila was stupid. I think every single thing she did was justified to her...And she really was terrifically in love."[12] For the role of Lila, Simon wanted Diane Keaton, but May thought the intended contrast between Jewish and gentile wouldn't be strong enough.[2]

Lenny's behavior as a classic nebbish Jew is thoughtless, as he leaves Lila high and dry on their honeymoon. Charles Grodin said afterwards that although he played the character with full sincerity, he had "pretty much indelibly stamped [himself] into the moviegoing public's consciousness as a jerk."[2] Still, he said, many viewers misread the film as an illustration of precisely Jewish annoyances and not as critique: "The number of men who tell me how much they loved the movie and how much they identified with the character, while flattering, is also somewhat frightening."[2]

The final moments of the film depict Lenny failing to communicate with Kelly's gentile family. It highlights how he gave up his personal cultural traditions, and how he misses them. Having walked down the aisle to Kelly as a large crucifix hung overhead, Lenny sits on the couch by himself, swimming in a sea of Christianity, listless and alienated as ever.[11]

The film has received almost universal praise from critics. Rotten Tomatoes gives the film a critic score of 91% and an audience score of 73%.[13] Notably, The New York Times declared it to be "a first-class American comedy, as startling in its way as was The Graduate."[14]